Abstract
A series of 9-aryl-hexahydroacridine-1,8-diones are synthetized with good to excellent yields (50–99%) via a one-pot four-component reaction of dimedone, aromatic aldehydes and ammonium acetate in the presence of 4 Å molecular sieves modified with iron(III) as an efficient heterogeneous catalyst, in ethanol. The process offers the advantages of high yields, mild reaction conditions and easy work-up procedure. The catalyst can be reused without significant loss of activity.Graphic
Highlights
During the past years, multicomponent reactions (MCRs) have emerged as valuable and efficient tools in the hands of synthetic organic chemists, since they have several advantages over the classical synthetic strategies
In this paper we present a simple method for the one-pot four-component synthesis of 9-arylacridine-1,8-dione derivatives from dimedone, aldehydes and ammonium acetate in the presence of a slightly basic, 4 Å molecular sieves-supported iron catalyst (Fe3+/4A)
We investigated the structure of the F e3+/4A catalyst by scanning electron microscopy (SEM)
Summary
Multicomponent reactions (MCRs) have emerged as valuable and efficient tools in the hands of synthetic organic chemists, since they have several advantages over the classical synthetic strategies. Acridinediones are a highly important class of organic compounds, since they possess a wide range of pharmaceutical and biological activities such as a positive ionotropic effect promoting the entry of calcium to the intracellular space [2], anticancer activity [3], enzyme and tumour cell inhibition [4], antimicrobial activity and cytotoxicity [5] They have structural similarity to 1,4-dihydropyridines (1,4DHPs), which are well known intermediates in the synthesis of several pharmaceuticals including those for the treatment of hypertension and cardiovascular diseases [6]. Acridine1,8-diones can be used as laser dyes with very high lasing-efficiencies [7, 8] Due to their importance, several strategies have been developed for the synthesis of 9-aryl-acridine-1,8-diones, including the thermal reaction of dimedone, different aromatic aldehydes and aqueous ammonia in ethanol [9], the microwave-irradiation-aided solvent-free reaction of dimedone and an aldehyde using alumina supported ammonium acetate and catalytic N,N-dimethylformamide [10],. Measurement, the samples were evacuated at 110 °C for 24 h
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